As soon as she arrived into her new Sergeant's office, Hailey was nervous. He'd requested her specifically from Robbery-Homicide, but she'd thought she'd made a fool of herself in front of the infamous Hank Voight. Instead he looked past her meritorious promotion and told her he wanted her on his hand picked team.
Even her Sarge in her last unit just treated her like an officer, an undercurrent of tension because she hadn't worked up the ranks like everyone else. Having to keep her undercover stint a secret was painful, but Voight hadn't cared. He knew she could do her job, and he let her at it. He introduced her to Erin, and their partnership could have been good if she hadn't taken the FBI job.
But Jay was her partner, her North Star. It was incredibly difficult at the start, he blamed her for who he thought was the love of his life leaving. She thought love was sweet, but insincere. It was a four letter word that she never wanted to hear, the word a scar like one from a bullet.
Hailey had always, always, always, been really good at compartmentalising her life. She could keep everything in nice little boxes. Work was work, home was home. But Intelligence changed all of that. Instead of leaving work when she left the precinct, she began to go for beers with her workmates after cases. A few drinks wasn't the most unhealthy thing they could do, especially when faced with what they saw every day. And she and Jay got closer, learning how they interacted and how they could play off each other's strengths.
The moment she realised she was developing feelings for him - feelings more than just him being her partner - was after she and Adam broke up. Adam's heart was never in it, he may have wanted to move in together but she knew they wouldn't be able to work and live together. And for both of them their work was more important than the relationship. His final hug of their relationship was filled with understanding and acceptance, and it made her feel better about the situation.
But that night, when she should have been miserable but wasn't, Jay came over with a bottle of nice whiskey, and they sat on her couch watching the Blackhawks game and staring out the window over Lake Michigan at the water. His arm was up on the back of the couch, and she could see the two of them there, possibly even growing old together in the future. And it scared her. Her background meant that she ran from anything like this. But this time she sat up and poured them both another drink, and gave Jay blankets and pillows to sleep on her couch.
Vanessa was the first to realise the depth of her feelings, asking her in that hospital waiting room if she loved Jay. And she kind of answered, but she could have left the "he's my partner" off it. But Love was a scary thing, it meant pain and it never meant goodness. So she shoved it down until she was home from New York, and her feelings were too strong to let go. She couldn't leave Jay. She could double her salary, move to New York, join a team that would make a difference countrywide…but she couldn't leave her team. The friendship that was growing between her and Kim, the easy camaraderie of the entire team, the wisdom Voight had started to give her now that he was changing how he did policing. And she couldn't ever leave Jay. If he left their partnership that was fine, but she couldn't leave him.
That night in the bar on the lake when he heard her double meaning and reached down and kissed her. She'd wanted it since that night she and Adam ended, and it was happening. He tasted of the liquor they'd shared, and they walked down the waterfront, his arm around her shoulder. To anyone else in the world they were two lovers, that easy familiarity that was grown between years of knowing each other. Except it was because they'd been friends for so long and it just made sense.
They'd fallen into bed together, and then fallen into living in between two apartments. The morning he admitted he loved her was the most terrifying of her life. She knew that was the emotion she felt when she was with Jay - the feeling of safety and security, of knowing he'd never raise a hand to her. But those words always came with "I'm sorry" and "I'll never do it again" but then it did happen, again and again and again. So she ran. And he let her run and when she was ready to tell him everything he was there and he believed in her and believed that she could do it and she deserved more than what she gave herself credit for. He just held her as she let her final defence down and sobbed for Becca and her ordeal, for Annie having to be so brave at such a young age for her best friend, for twelve year old Hailey whose only security at that age was a cantankerous cop who helped her and made her feel whole even while she was praying for her father to die from his injuries.
And then they were wondering why they still paid separate rents, with half their things in each other's apartments, two coffee machines, four toothbrushes, two hairbrushes, two full sets of toiletries. They picked Haileys because the location was better and it was slightly further away from Will so he wouldn't interrupt them, and moved their boxes in together. Their friends and colleagues moved with them, pizza shared between the group as Hailey showed her best friend's officially adopted daughter how to fold a napkin into a swan like she did in the restaurant. Being waved goodbye as aunt Hailey and uncle Jay, holding each other as they waved everyone off. Lying in bed, wide awake and wondering if she was reliving her mother's mistakes when Jay wrapped his arms around her and whispered that he loved her and he was so proud of her for doing what was hard.
Filling in papers at work, dividing bills, realising they were able to save money at last and deciding to start saving for a house of their own eventually. And then the night where Jay brought her back to that bar where everything started, ordering each of them the same whiskey as before. Her drinks tastes had changed, she'd left hard liquor in the past in place of beers she could taste and enjoy instead of attempting to get drunk and forget. But they toasted to five years as partners and eighteen months as lovers, and Jay pulled out a ring box to show her his mother's stones in a new setting all for her. He didn't get down on one knee, he knew the gesture was pointless for her. Instead he opened it and put it in the middle of the table, asking her would she marry him and let him make her happy, so she said yes and wore it proudly, signifying that she was Jay Halstead's and he was Hailey Uptons, and nothing could separate them.
Until that stupid fight at 2.30, him asking if she wanted her parents to be at the wedding and she shot it down immediately. Seeing the list of Halstead family and aunts and uncles, the cousins who lived in Ireland and wouldn't get an actual invitation but would get a "we're getting married and we know you can't fly to Chicago but we're remembering you" card. Her insecurities hit the roof, that she was marrying this man who loved so deeply and so brightly, and all she would do was dim his brightness. She'd seen him fight past the darkness of his PTSD diagnosis, of freezing at fireworks and after a gun was shot to where he was today. She couldn't do that to him, so she ran back to the shore that had been her guide their entire relationship.
She stood staring out at the dark water, feeling his presence behind her. This was the end. She'd ruined her happiness because she was broken. Hailey Upton had never learned what love was at a parent's knee, instead knowing what masqueraded as it. Of course she could never love someone like Jay the way he deserved to be loved. Her tears were slipping through her eyes as she realised everything that she'd deprived him of because he had to think he'd fallen in love with this shell of a woman.
But instead he held her, his arm around her shoulders as they both stared into the water. When he spoke his voice was husky, his tears evident.
"I'm never leaving you alone, Hailey. I fell in love with the careful daughter of a careless, awful man, and you are the best person I could have fallen for. Every time I look at you it's like the first time I'm seeing you again. You are the best thing that's ever been mine."
She turned into him the same way she had when she admitted she loved him, her eyes glassy as she did. They didn't say the words often, content in the knowledge that they knew the truth even if they didn't say it. They walked home slowly, relishing the comfort of holding onto each other, that Hailey could hold him and be held and know she was ok. He wasn't going to follow his words with the terror they'd held all her childhood. And as they got into bed, she in his shirt so she had an extra dose of his scent, the final thing she heard before drifting off was "I love you."